Effect of Specific Solute-Solvent Interaction and Electron Donor-Acceptor Substituents of Novel Pyrazolo Naphthyridines on Fluorescence

Heterocyclic orthoaminoaldehyde such as 4-amino-3-(4-phenyl)-1-phenyl-1H-Pyrazolo[3,4-b]pyridine-5-carbaldehyde was synthesized by multistep reactions involving reduction of azido derivative 2 with LAH to yield aminoalcohol 3 and oxidation of it with MnO2 to aminoaldehyde 4.The pyridine ring annulated on to 4 by Friedlander condensation using acetophenones in presence of base to obtained pyrazolo[3,4-h][1,6]naphthyridine 5 in excellent yield. Study of photophysical properties of 5 revealed that the absorption and emission of them depends up on the substituents present on benzene ring in newly annulated pyridine ring.